A novel asymmetric route to the 1,3-disubstituted tetrahydroisoquinoline, (-)-argemonine

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4607-4610

  Munchhof, Michael J ^a   Meyers, A I ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARGEMONINE; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029946058     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960110h     Document Type: Article

References (11)

1. (a) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399.
2. (b) Munchhof, M. J.; Meyers, A. I. J. Org. Chem. 1995, 60, 7084.
3. (c) Munchhof, M. J.; Meyers, A. I. J. Org. Chem. 1995, 60, 7086.
4. For previous synthesis of argemonine see: (a) Nomoto, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1982, 19, 1113. (b) Rice, K. C.; Ripka, W. C.; Reden, J.; Brossi, A. J. Org. Chem. 1980, 45, 601.
5. For previous synthesis of argemonine see: (a) Nomoto, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1982, 19, 1113. (b) Rice, K. C.; Ripka, W. C.; Reden, J.; Brossi, A. J. Org. Chem. 1980, 45, 601.
6. Palmquist, U.; Nilsson, A.; Pettersson, T.; Rolán, A. J. Org. Chem. 1979, 44, 196.
7. Meyers, A. I.; Boes, M.; Dickman, D. A. Angew. Chem., Int. Ed. Engl. 1984, 23, 458.
8. Burgess, L. E.; Meyers, A. I. J. Org. Chem. 1992, 57, 1656.
9. Hubert, J. C.; Wijnberg, J. B.; Speckamp, N. C. Tetrahedron 1975, 31, 1437.
10. Chamberlin, R. A.; Nguyen, H. D., Chung, J. Y. J. Org. Chem. 1984, 49, 1682.
11. D -214 (c = 3.3, EtOH).